#57 | From “I Never Wanted to Teach” to Transforming 50+ Schools: Kyle Sumrow, Robby Cobbs, & the Real Work Behind EdTech

This is the story of two educators who never planned to become educators, and ended up building an edtech nonprofit that’s served 50+ schools in Puerto Rico. Robby Cobbs and Kyle Sumrow break down the “international teaching cheat code,” the masks they wear as leaders, and how they turned frustration into a system that helps schools build real tech plans (not PDFs that die in a Google Drive). Listen and apply these takeaways to your school tomorrow:Why “dignity” matters more than “respect”, and how that mindset changes your classroom and your leadershipFairness vs. equality (the glasses example) + why “kindness all the time” isn’t soft, it’s strategicThe power of community when you’re far from home: international schools, brotherhood, and what “family” can mean when it’s built (not forced)How TechMySchool was born in Puerto Rico, no libraries, not enough books, and one question that sparked a movement(0:00) Class in session + meet Robby Cobbs and Kyle Sumrow(0:30) Robby’s origin story: from “no teacher dreams” to finding home in schools(5:30) Teaching in inner-city schools + the travel bug that changed everything(7:00) International teaching explained (housing, flights, medical, taxes)(13:35) Kyle’s journey: music school → bus driver → subbing → “this is what I want to do”(18:50) Teaching as the ultimate learning hack (bio → CS → film → audio → auto)(30:10) “Family” in international schools—when community builds itself(35:40) The “mask” exercise: what you show vs. what you carry as a leader(38:00) Kyle’s mask: dignity, fairness, growth and the unseen leadership habits(41:30) Robby’s mask: confident leader, service, empathy and the hidden frustration behind nonprofit work(52:20) TechMySchool origin story: Puerto Rico schools, no libraries, and scaling from 1 school to 50+(55:15) “Week Without Walls” + bringing students to other places for perspective shifts(1:09:50) How to support + the Caribbean edtech conference (April 10–11)(1:11:10) TechPlanGenie: AI-powered tech planning + accountability + end-of-year reportConnect with Robby Cobbs + Kyle Sumrow / TechMySchool:Website: techmyschool.orgInstagram/Facebook: Tech My SchoolCaribbean EdTech Conference: April 10–11Join/Contribute to our Young Men’s Conference: https://everforwardclub.orgJoin our Skool Community: https://www.skool.com/efc-young-mens-advocates-2345Submit Questions, Reflections, or Episode IdeasEmail us: [email protected] your mask anonymously: https://millionmask.org/Connect with Ashanti BranchInstagram: https://www.instagram.com/branchspeaks/Facebook: https://www.facebook.com/BranchSpeaksX: https://x.com/BranchSpeaksLinkedIn: https://www.linkedin.com/in/ashantibranch/Website: https://www.branchspeaks.com/Support the Podcast & Ever Forward ClubHelp us continue creating spaces for young men to be seen, heard, and supported:https://podcasters.spotify.com/pod/show/branch-speaks/supportConnect with Ever Forward ClubInstagram: https://www.instagram.com/everforwardclubFacebook: https://www.facebook.com/everforwardclubX: https://x.com/everforwardclubLinkedIn: https://www.linkedin.com/company/the-ever-forward-club/#unmaskingwithmaleeducators #millionmaskmovement #takingoffthemask #totm #doace